Hydrochloric Acid → 3-(Oxan-2-yl)propanoic acid
Reaction equation
[OH-].[Li+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([O:13]C)=[O:12].Cl>O1CCCC1>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 2M aqueous solution of lithium hydroxide (4 ml) was added to a solution of methyl 3-(tetrahydropyran-2-yl)propanoate (Preparation 25, 460 mg, 2.67 mmol) in tetrahydrofuran (16 ml) and the reaction mixture was heated under reflux for 10 h. The cooled reaction mixture was acidified with 2N aqueous hydrochloric acid to pH 1 and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine (30 ml), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a colourless oil (460 mg, 67%).
Workup
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 10 h
- customThe cooled reaction mixture
- extractionextracted with ethyl acetate (3×50 ml)
- washThe combined extracts were washed with brine (30 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3769e7c605bd41f9975ef254e9452731
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610711B2
Reaction notes
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